Kavain

Kavain
Names
	Preferred IUPAC name 4-Methoxy-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one
	Other names (E)-4-Methoxy-6-styryl-5,6-dihydro-2H-pyran-2-one; Kawain
Identifiers
CAS Number	500-64-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	4520267 ;
ECHA InfoCard	100.007.189
KEGG	D08096 ;
PubChem CID	5369129;
UNII	W1ES06373M ;
CompTox Dashboard (EPA)	DTXSID5033595 ;
	InChI InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+ Key: XEAQIWGXBXCYFX-BQYQJAHWSA-N ; InChI=1/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+ Key: XEAQIWGXBXCYFX-BQYQJAHWBH;
	SMILES COC1=CC(=O)OC(C1)/C=C/C2=CC=CC=C2;
Properties
Chemical formula	C14H14O3
Molar mass	230.263 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Kavain is the principal kavalactone found in the roots of the kava plant (Piper methysticum), where it contributes significantly to the plant's psychoactive and anxiolytic effects.

Kavain exhibits anticonvulsant properties by modulating voltage-dependent sodium and calcium channels, and it may influence mood and anxiety through reversible inhibition of monoamine oxidase A and monoamine oxidase B, potentially affecting serotonin, dopamine, and norepinephrine signaling. Although it does not bind to the benzodiazepine site of GABAA receptors, kavain potentiates GABA activity at extrasynaptic α4β2δ GABAA receptors and overlaps with the modulatory pathways of certain general anesthetics. It also shows weak sodium antagonism, strong L-type calcium channel blockade, and enhances early potassium currents, suggesting mood-stabilizing effects akin to lamotrigine.

Its precise mechanisms remain under investigation, but its activity across multiple pathways makes it a promising candidate for drug development targeting ion channels, P-glycoprotein, cytochrome P450, and cyclooxygenase enzymes.